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A triphenylphosphine mediated photo-rearrangement and methanol addition of aryl chalcones to 1-propanones

Sun, Qiu, Yao, Chang Jiang and König, Burkhard (2015) A triphenylphosphine mediated photo-rearrangement and methanol addition of aryl chalcones to 1-propanones. Photochemical & Photobiological Sciences 14, pp. 948-952.

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Abstract

Aryl chalcones rearrange and add methanol giving substituted propane-1-ones upon UV-A irradiation in the presence of PPh3. We propose two possible mechanisms for this photo-rearrangement. The reaction involves either the formation of a phosphine-carbonyl intermediate, nucleophilic addition of MeOH and 1, 2 aryl migration or the formation of ylide and carbene intermediates. Intermediates trapped from the reaction mixture support the first mechanistic hypothesis.


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Item type:Article
Date:2015
Institutions:Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Projects:GRK 1626 Chemische Photokatalyse
Identification Number:
ValueType
10.1039/c5pp00009bDOI
Dewey Decimal Classification:500 Science > 540 Chemistry & allied sciences
Status:Published
Refereed:Yes, this version has been refereed
Created at the University of Regensburg:Yes
Item ID:31351
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